OhHello with Jeremy Bloom

Jackelyn Keller, a marketing leader, strategist, and educator—and Founder of Jackwell Partners, a marketing consultancy—shares her journey from sales assistant to CMO and what it taught her about trusting your instincts. Known for translating complex technology into clear, actionable strategy, she explores career pivots, building confidence without certainty, and why mentorship and relationships often matter more than resumes. Takeaways Confidence isn’t about having all the answers–it’s trusting that you’ll figure it out. Career growth comes from trying new things rather than staying where you’re comfortable. Relationships often matter more than what’s on your resume. Mentorship works best when it’s rooted in empathy and active listening. Taking care of yourself shapes how you show up at work and in life. Chapters 00:00 Introduction to Jackelyn Keller and her background 02:30 Building a career across marketing, teaching, and entrepreneurship 06:10 Knowing when to push through versus when to pivot 07:45 Taking risks before feeling ready 10:00 Redefining confidence as self-trust 11:40 Overcoming fear of public speaking through teaching 14:15 Mentors who shaped her career 16:20 What makes a great mentor 17:20 Why leaders struggle to ask for help 18:20 Managing self-doubt and personal pressure 20:00 The importance of outside perspectives 22:20 Advice for early-career professionals 23:15 The value of mentorship and community

Jason Loehr, a data and AI advisor with experience across companies like Camping World and Brown-Forman, joins Jeremy Bloom to discuss how leaders can combine technology, empathy, and critical thinking to navigate digital transformation. They explore Jason’s early experience launching one of the first online catalogs, how consumer-first thinking shaped his career, and why AI should empower people rather than replace them. Jason also shares insights on leadership, curiosity, and how organizations can use data and learning agendas to make better decisions. Takeaways Early digital innovation showed Jason that understanding customer lifetime value can reshape how companies view new technology. Successful digital transformation happens when organizations prioritize consumer experience over internal convenience. AI should free up human time for deeper critical thinking rather than replace human roles. Empathy and creative friction are essential for solving complex problems and building better ideas. Organizations make better decisions when they focus on the questions they need answered before gathering data. Democratizing data helps teams collaborate and solve problems faster across the organization. Leaders should automate predictable work, elevate human judgment, and optimize decision velocity. Technology itself is not the disruptor but the tool that enables meaningful disruption. Chapters 00:00 Jeremy welcomes Jason and introduces his background in digital transformation and marketing. 01:00 Jason shares his career journey from early e-commerce to working with major global brands. 03:30 Why consumer-centric thinking should guide technology and digital decisions. 05:30 Leadership traits, including curiosity, relationship building, and humility. 08:30 How AI and empathy work together in the future of work. 10:20 Using data and learning agendas to improve decision making. 13:00 A leadership framework automates predictable tasks, elevates human insight, and optimizes velocity. 14:00 The mentors and relationships that shaped Jason’s career. 16:00 Why leaders must stay intentional when adopting new technologies.

In this engaging conversation, Jeremy Bloom and Jay Wolff explore the intricacies of leadership, mentorship, and the importance of human connection in the digital advertising industry. Jay shares his journey from the early days of digital advertising to his current role, emphasizing the significance of empowering others and building meaningful relationships. The discussion highlights the value of networking, the role of mentorship, and practical advice for motivating teams and fostering a supportive work environment. Takeaways Leadership is about connecting people and empowering them. The journey to leadership involves learning through experience. Mentorship can come from various sources, including family and colleagues. Networking should be genuine and reciprocal, not transactional. Small gestures can have a significant impact on relationships. Understanding individual motivations is key to effective leadership. Creating a supportive environment fosters psychological safety. Involvement in local organizations can enhance career growth. Building a personal brand is essential in today's professional landscape. Empowering others leads to a more successful and cohesive team. Chapters 00:00 Introduction and Background 02:42 Defining Leadership and Team Building 05:40 The Journey to Leadership 08:41 Mentorship and Influences 11:44 The Importance of Networking 14:21 Motivating and Empowering Teams 17:31 Final Thoughts and Advice

Ajinkya “Jinx” Joglekar joins Jeremy Bloom to share what he learned leading marketing at Dish and Sling, why he decided to take the leap into consulting after 20+ years in corporate, and how curiosity became the skill that helped him “punch above his weight” early in his career. They also dig into what real mentorship looks like, how leaders can build a culture of learning across teams, and why great advertising is not just creative and media but also the sales experience. Takeaways  Your corporate career can be the venture capital that funds your future risk-taking. Curiosity lets you lead and influence even before you have a title or direct reports. Great advertising only works when creative, media, and the sales experience are connected. Leaders build learning cultures by meeting every level of the team and making collaboration unavoidable. Mentorship programs work best when they are supported from the top but driven organically from the ground. Chapters  00:00 Jinx introduces himself and his background leading marketing at Dish and Sling. 03:05 Why he left the CMO seat to bet on himself and start consulting. 06:40 The mentor who gave him his first real marketing start and taught him scrappy fundamentals. 12:10 The moment he realized curiosity is a career advantage that helps you punch above your weight. 14:40 How to build a culture of learning through one-on-ones and cross-team collaboration. 18:10 Advice for emerging marketers and sellers: don’t stay in your lane and use your network. 20:05 How organizations can create mentorship programs that work without feeling forced.

Jeremy Bloom and Scott Hess, Chief Marketing Officer of Starcom and Chief Marketing Officer of Publicis Media, discuss the significance of the Chicago Advertising Federation's Career Day, the importance of mentorship and networking in the advertising industry, and personal experiences that shaped their careers. They reflect on the joy of working in advertising and the opportunities available for young professionals entering the field. Takeaways Scott Hess is the Chief Work Officer of Publicis Media. The Chicago Advertising Federation's Career Day is crucial for networking. Mentorship can significantly impact career paths in advertising. Career Day demystifies the advertising industry for young people. Networking events provide access to industry leaders and opportunities. Scott's son found joy in advertising after initially pursuing engineering. The advertising industry offers diverse career paths and opportunities. Personal connections can lead to job opportunities and mentorship. The excitement of young professionals can reinvigorate seasoned veterans. Chicago's winter can be a downside, but the city has much to offer. Chapters 00:00 Introduction and Background 02:43 The Importance of Career Day 05:37 Mentorship and Networking in Advertising 08:50 Personal Experiences and Career Paths 11:38 The Joy of Working in Advertising 14:37 Conclusion and Upcoming Events